3-methyl-4-nitrophenol

Synonyms: "4-nitro-m-cresol", "4-nitro-3-cresol", "5-hydroxy-2-nitrotoluene", "4-nitro-3-methylphenol", "2-nitro-5-hydroxytoluene", "4-nitro-5-methylphenol", "p-nitro-m-cresol", "4-nitro-1-hydroxy-3-methylbenzene", "5-methyl-4-nitrophenol", "3-methyl-4-nitro-phenol".

Source: 3-methyl-4-nitrophenol is a major metabolite of fenitrothion.

Identifiers:

IUPAC Name: 3-methyl-4-nitrophenol
CAS Number: 2581-34-2
PubChem ID: 17412
InChiKey: PIIZYNQECPTVEO-UHFFFAOYSA-N
Canonical SMILES: CC1=C(C=CC(=C1)O)[N+](=O)[O-]

Structural Properties:

Molecular Formula: C₇H₇NO₃
Molecular Weight: 153.137

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 3
Number of atoms different from hydrogen: 11

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2D structure (.sdf)
3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
3D structure (.pdbqt)

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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Furuta C, Noda S, Li C, Suzuki AK, Taneda S, Watanabe G, Taya K. 2008. Nitrophenols isolated from diesel exhaust particles regulate steroidogenic gene expression and steroid synthesis in the human H295R adrenocortical cell line. Toxicol Appl Pharmacol 229(1):109-120. DOI: 10.1016/j.taap.2008.01.026. URL: https://www.sciencedirect.com/science/article/pii/S0041008X08000549.
Li C, Taneda S, Suzuki AK, Furuta C, Watanabe G, Taya K. 2007. Effects of 3-methyl-4-nitrophenol on the suppression of adrenocortical function in immature male rats. Biol Pharm Bull 30(12):2376-2380. DOI: 10.1248/bpb.30.2376. URL: https://www.jstage.jst.go.jp/article/bpb/30/12/30_12_2376/_article.
Taneda S, Mori Y, Kamata K, Hayashi H, Furuta C , Li C, Seki K, Sakushima A, Yoshino S, Yamaki K , Watanabe G, Taya K, Suzuki AK. 2004. Estrogenic and anti-androgenic activity of nitrophenols in diesel exhaust particles (DEP). Biol Pharm Bull 27(6):835-837. DOI: 10.1248/bpb.27.835. URL: https://www.jstage.jst.go.jp/article/bpb/27/6/27_6_835/_article.